Wine & Cheese Cruise

Wine, cheese, skyline. Need we say more?

Wendella's Wine & Cheese Cruise is pure Chicago indulgence. Because what pairs better with this city's iconic skyline than a curated selection of local wines and cheeses?

This isn’t a rush-around kind of ride. On this wine tasting cruise, we'll take you down the Chicago River for up-close views of the city's architectural gems, then glide onto Lake Michigan, where the skyline opens up in all its golden hour glory. And believe us—you won't leave hungry or thirsty.

Gentle music and great service set the tone. It's like a floating picnic, but a little more luxe. Perfect for dates, foodie nights out, or any excuse to toast something ("To Chicago!"). 

Most guests head to the open-air deck for the views, but if the breeze picks up, you can cozy up in the climate-controlled lounge. There’s also a full-service bar on board in case you want to branch out from your wine flight. 

It’s laid-back, lovely, and just the right amount of fancy with the city sparkling all around you.

• Curated wine tasting and hors d’oeuvres
• Open-air seating and covered lower deck
• Friendly crew to answer your questions
• Iconic skyline views
• Restrooms on board

We depart rain or shine; Chicago weather is unpredictable, but our boats are built for it. We recommend arriving at the dock 30 minutes before your scheduled departure time since boarding typically begins 15 minutes prior. All bags are subject to screening, and outside alcohol or weapons are not allowed. Please bring valid ID with you, as this cruise is 21+. Tickets are non-refundable and non-transferable after the scheduled departure time. Not sure where to go? Head to 400 N Michigan Avenue, right by the historic Wrigley Building at the northwest corner of the DuSable (Michigan Avenue) Bridge. For additional info chat with us, or give us a call.

We have a selection of local favorites available for purchase, including snacks, candy, soft drinks, beer, wine, hard seltzer, cider, and cocktails. Find our full Menu here.

Our boats are wheelchair accessible from our West Dock, with a ramp to the upper deck. All of our boats have ADA-compliant restrooms. Some of our boats have an elevator from the upper to lower deck, where the bar and restrooms are located. Please call us in advance on 312-337-1446 so we can assist.